Operation Wingman
by withgirl
Summary: Emma keeps coming up with reasons why her and Regina can't be together and Henry decides to systematically disprove each one [Emma X Regina pairing] THIS IS SWANQUEEN AND HOOK IS IN THE STORY!
1. Chapter 1

"Do it now," Henry whispered, trying to covertly look over to the counter at the brunette ordering her coffee-to-go.

Emma instantly felt her throat constrict at what he was suggesting and began to vehemently shake her head, "in what world would Granny's be the best place for this?"

"What would be the best place?" the boy shot back with a grin on his face. Since he had first met Emma, he had always seen her as the completely fearless saviour. She had travelled to the Enchanted Forest, Neverland and even through time without a single hint of nerves, let alone fear.

"Somewhere more private…where everyone won't see the rejection," the blonde mumbled, looking down at the table.

"What are you two talking about?" another voice asked before Henry could yet again try and convince his mother that she wouldn't be rejected.

The boy swallowed hard and smiled suspiciously at his other mother, "we were just talking about who would win in a fight, Hulk or Loki…"

Regina tilted her head and looked between them with narrowed eyes, "the answer is obviously the Hulk."

"That's what I said," Emma said far too quickly to be considered normal.

"In the Avengers, it was after the portal was closed and he didn't have his sceptre, so he wasn't technically at his full power," Henry said quickly, hoping desperately that his brunette mother would buy it.

She clearly didn't, but when she looked over to the blonde on the other side of the table, she saw that she was uncomfortable with the topic. Instantly, she decided her best friend, or whatever were to each other, would tell if she wanted to. The mayor saw no need to pry, as long as neither of them were in danger, they were entitled to some lies.

"Very well, I'll leave you to your debate and I'll see you after work," she said with a small amount of amusement in her voice as she rose from her chair. Simultaneously, she grabbed her coffee and planted a kiss on her son's forehead, the woman offered the blonde a smile by way of goodbye, before making her way to the door.

Once the bell rang out to confirm that she was truly left, Henry turned back to his other mother and shook his head.

"What?" the saviour asked dramatically.

"How is it that we can have breakfast as a family, but you can't even ask mom out on a date?"

The blonde felt her throat constrict again and she just shook her head, "we've been through this Henry. Her relationship with Robin only just ended…"

"Three months ago, ma, it ended three months ago. Plus, mom was planning to break up with him anyway, she thanked you for bringing Marian back, remember?"

The sheriff blew out a breath and looked away from her son again, sometimes she really hated how astute he was. The real reason that she had refused to cooperate with Operation Mongoose was because she was afraid. Henry was convinced that his mother wouldn't need to find the author anymore, not that she was really looking anyway, if Emma would just ask her out. In his mind, they made the perfect couple, though the saviour had a feeling that it had something to do with him being able to refer to them as his parents. Even if he would never admit it aloud (mostly because he didn't want to hurt Regina again) the boy longed for a stable parenting unit, probably even more so since he lost his father.

The bell over the door rang again and Emma felt her palms begin to sweat at the thought that maybe Regina forgot something. She often worried that Henry would take it upon himself to arrange their date and he certainly seemed in the mood to do so right now.

However, her shoulders instantly relaxed when she saw that the new arrival was no other than Killian Jones. Though the pair of them had explored a possible romantic relationship, it had quickly fizzled, especially since he had far more interest in Tinkerbell. It was for that reason that the pirate was now her unofficial best friend. He often complained about not being able to hold the title officially because the saviour wouldn't just ask her 'actual' best friend to be her girlfriend.

"Hey Swan," he said with a smirk, instantly knowing that the expression she was wearing meant that Henry was nagging her about asking Regina out.

Emma blew out a breath of frustration when she realised that she was now out-numbered as the pirate fell into the seat next to her son, "I'm really not in the mood to talk about this, Hook."

Hook and Henry exchanged a look, before the younger of the two asked, "do you not like mom?"

"You know that I more than like her," Emma shot back quickly, obviously insulted by the insinuation that her feelings were not real.

"Then why are you avoiding the inevitable, Swan?" Captain Hook asked, his smirk having fallen away when he realised that she was genuinely upset about this.

"Because if she says no, then nothing will be the same again," the blonde whispered with crossed arms, her eyes firmly staying on her food.

"And nothing will be the same _when_ she says yes," Henry replied, suddenly feeling bad for not noticing his mother's insecurities.

The saviour just remained in silence as she considered this, but she just shook her head again, "when I brought Marian back, I thought I had lost Regina as a friend. Before she thanked me, I was so worried that she would never talk to me again. I just wouldn't be able to handle it if things got awkward between us because I can't deal with a stupid crush."

"It's not just a crush, ma," the brunette boy argued, "you told me that you love her, so why can't you just tell her?"

Emma swallowed hard and looked up at Killian, hoping that he would understand that she didn't want to have to explain what she mentally called 'orphan issues'.

The pirate instantly understood and said, "I believe that sheriff has a shift to get to, lad."

Henry opened his mouth to protest, but the man stood up, motioning for him to do the same.

The boy rolled his eyes, though he wasn't too frustrated. At least when Killian watched him during the school holiday, he didn't have to deal with spending the day listening to his uncle cry.

"I'll see you later, ma," he mumbled, kissing her on the cheek.

Killian smiled at the blonde who mouthed 'thank you', before he put his hand on the lanky boy's shoulder and led him out of the diner.

"Why did you do that?" Henry grumbled once they fell into stride with each other on their way to the harbour.

"If Swan's love life was as simple as you're making it out to be, the two of them would already be married, lad," the pirate chuckled.

Henry let out a huff, but still nodded his agreement, "so what do you suggest I do?"

"Well, you know that Emma loves Regina, but do you know for a fact that madam mayor feels the same way?"

The teen furrowed his brow in thought.

He hadn't really questioned whether his brunette mother felt the same way, since in his mind, their relationship made complete sense. There was no real reason to question it, since they were so obviously meant for each other. But he now saw that telling the savour that they made a good 'story' probably wasn't the best way to help her get past her nerves.

"I guess I don't know for a fact," he sighed, "but you can just tell when they look at each other, you know?"

"Oh, I definitely know," he chuckled, "I believe that the whole town knows. Emma has finally found a family, Henry, I'm sure that she wouldn't want anything to change how things are now. Even if there is a chance that things would be better, there is also the chance that things would be worse…."

The boy frowned, but still nodded, "okay, so what do you thing we should do?"

Killian raised his eyebrows, usually he would question why he was automatically involved. But since he had become a kind of father-figure for the boy, he had become pretty used to it.

"How about…Operation Wingman?"

"Wingman?" the brunette asked in confusion, he had heard the term before, but he wasn't one hundred percent sure that he knew what it meant.

The pirate laughed lightly, and replied, "I suppose the first step would be ensuring that the wingman knows what a wingman is."

* * *

Henry looked between his mothers as they talked about their days at work over their usual family dinner.

In that moment, he thought about how odd it would be for someone who didn't know them to find out that the three of them weren't really a family. They were supposedly two best friends/co-parents who shared a son. Which was something that he fully intended to change.

Thinking back to what Killian had told him, a smile spread across his face when he realised that he could easily check step one off the list right now. The pirate had pointed out that one of the issues might lie in the fact that Emma didn't know for sure what the former Evil Queen's sexuality was. Most people knew for sure, since it wasn't as if she was trying to hide it, but it seemed as though the blonde was trying to come up with excuses for not risking their friendship.

Swallowing a bit of mashed potato, he decided that now was as good a time as any.

As soon as there was a silence if the blonde and brunette's conversation, Henry said, "mom, can I ask you something?"

Regina looked across the table at the boy, she was confused for a moment since he never asked permission to ask a question. Then it occurred to her that he sounded slightly timid and his age registered in her mind.

Taking a deep breath, she tried to convince herself that she was ready for this, but the fact was that she wasn't. She had actually been putting off talking with Emma about the issue, she didn't know whether she should be the one to broach the subject or wait for Henry to come to either one of them.

"Of course you can, sweetheart," she replied in a rather uneven voice.

Emma eyed their son cautiously, she had a feeling that what Regina thought he was going to ask wouldn't be coming up, at least not this year. She only hoped that whatever he had planned wasn't to just come right out and tell the truth. That hope didn't stop images of Regina trying to explain to their son why she didn't want a relationship with the saviour and anxiety began to build in her stomach.

Henry smiled at Emma, before he looked back over to his brunette mother and asked, "what is a bisexual?"

Regina's eyes widened for a moment, she wasn't quite sure whether she was relieved or not. There was no reason that her son shouldn't get the answer that he wanted, but at the same time she was rather curious who introduced him to that term.

"Well, it's a word that describes a person who is romantically interested in members of both sexes, what brought this up?"

The brunette nearly let out a frustrated sigh when her words neither confirmed nor denied her sexuality, but he realised it would have been a rather for her answer to be 'me'.

It was for this reason that he knew he had to keep the topic going until he could naturally find a way to get her to say the words for Emma's benefit.

"Someone in the grade above me came out as gay so it made me curious about how accepting people in the Enchanted Forest were. I asked Killian and he said that you made being gay and bisexual legal when you became queen…I didn't realise that I didn't know what it meant until later…"

Emma rolled her eyes as she felt her 'superpower' go off. It wasn't like she needed it to tell her that the boy was lying, she had no doubt that this was exactly what Killian had told him to do.

However, after a moment, her eyes widened and she looked back over to Regina in a sort of awe. "you made it legal?"

The brunette tilted her head at the woman's surprise, "it was an archaic law that needed to be abolished," she shrugged, "I didn't really see it was a big deal at the time since there were not many who actually followed it anyway…"

The woman allowed the implications to speak for themselves, obviously the Evil Queen had bigger plans than abolishing out-dated laws, which most likely involved find new and inventive ways to murder Snow White.

"I guess that's one thing that makes the Enchanted Forest better than here," Emma laughed, trying to hide the fact that she had just found another reason to find Regina perfect.

"Just one?" the mayor asked, raising a perfectly plucked eyebrow in amusement.

"Electricity, in-door plumbing, Wi-Fi, TV, no bandits, no ogres, no beanstalks…"

The brunette held up her hand and laughed, "I get it, Emma, you didn't like the Enchanted Forest."

"I liked chimera," the blonde replied with a smirk, "is there any way you could get me some for my birthday?

The mayor just shook head and laughed while she picked up her glass of wine and took a sip.

Henry looked between them and rolled his eyes, it was honestly amazing how quickly the pair of them could get off track.

"I still don't get it, mom," Henry pressed, instantly receiving a warning look from his blonde mother, "is it like a fifty-fifty split, or do some bisexuals like one gender more than the other?"

Regina frowned, she wasn't exactly sure why he was so interested in this topic, but it wasn't a bad thing if she could stop him from believing common misconceptions.

"It's not about percentages, Henry, it's about the person. Being bisexual does not automatically mean that a person will be with more people than a straight or gay person. It just means that they are open to attraction to with a greater number of people, they still have to find the right person for them like anyone else has to."

The boy nodded slowly, covertly grinning when he thought of the perfect question, "I get it," he replied, "but how do you know so much about this, mom?"

The former Evil Queen tilted her head, she was sure that everyone in town knew, but then it occurred to her that she hadn't been with a woman in her son's lifetime and she like to believe that he wasn't old enough to pick up on the clues.

"I…I know because I am bisexual, Henry," she said slowly, trying to gauge his reaction, not that she had any idea what she would do if he disapproved.

The boy was about to smile and reassure her that it was more than okay with him, but he was interrupted by a choking sound.

Looking over to the saviour, he couldn't help but smirk as she held her hand over her mouth, trying to swallow her bite of food as gracefully as possible. There was a rather obvious hue of blush forming across her cheeks. Hearing Regina admit it out loud did make her dreams far less unlikely, but she there were still a million other reasons that she could think of why Regina would say no.

"Are you okay?" Regina asked.

The blonde just kept her mouth shut and nodded.

Regina tilted her head, she would have questioned her further if she hadn't just told her son something important.

Looking back over to the boy, she received the smile he had wanted to give her a moment ago.

Her shoulder's instantly relaxed and she rose from her chair, "I should go and get the dessert out of s

the oven."

Once she was out of ear-shot, Emma finally unsealed her lips and said, "was that Operation Mongoose?"

"Nope," the boy replied smugly, "Operation Mongoose was to find mom's happy ending, which I'm pretty sure I already have. So this is an operation to make you stop being so stubborn."

Emma blew out a breath of frustration and shook her head, "I'm not stubborn, I'm just realistic."

Before Henry could say anything in return, the distinctive clicking of heels alerted him to the returning of his mother, who slid regally back into her seat.

"The pie should be cooled soon," she announced looking between the pair.

"Awesome!" the other brunette replied somewhat over-enthusiastically, "can ma stay and watch a movie with us?"

Regina looked over to Emma, who seemed like she was contemplating something, and replied, "of course she can…"

"Actually, I had a really long day, I think I should just go," the blonde replied, shooting up out of her seat. "Thanks for dinner, it was really good…"

"…okay…" the brunette replied in confusion, looking over to Henry for an explanation.

The boy just shrugged as his blonde mother left and he fell back against his seat, letting out a huff, he realised that he would have to report that Emma might be even more stubborn than either of them thought possible.

* * *

Regina tried to focus on her laptop, but her mind seemed intent upon making the words on the report blur together.

It was almost as if her eyes knew that she would much rather be spending her time reprimanding Emma for getting popcorn on her couch. It was also rather a disappointment that she hadn't had the chance to 'accidentally' fall asleep on the younger woman's shoulder.

Instead, Henry had decided to go to bed early, no doubt he working through a new operation, and she had decided to go into her study and try and make a head start on her work for the next day. Now that she was looking at a page of numbers though, she couldn't stop herself from thinking about far more important things, i.e. her love life, or lack thereof.

With a huff, the woman closed her laptop and rose from her chair to go and pour herself a tumbler of apple cider.

She honestly had no idea what could possibly have made Emma run away so quickly, without having dessert no less. It hurt more than she had expected it to, mostly because she had yet to admit the depth of her feelings towards the sheriff, even to herself. She knew that she had certainly been attracted to the woman the moment she had laid eyes on her, but really, who wouldn't be? It was for this reason that she had spent much of her time disregarding what were quickly developing into a fully-fledged crush.

After Neverland, though, she found that it wasn't as simple to deny that it was more than mere physical attraction. During the missing year, she found that it wasn't just Henry she had missed with all of her heart.

However, she had met Robin and become convinced that she wasn't really in any position to deny fate. In her mind, being with Robin Hood made more sense than the Evil Queen ending up with the Saviour. No matter how close she was to admitting that she truly loved the woman, she had been constantly reminding herself that the blonde deserved better. It was for that reason that she had resigned herself to covertly stealing moments with the sheriff, which was why she was so peeved to have one of their family nights stolen away from her for no particular reason.

Downing the spicy liquid, she took a moment to compose herself before she went back over to her desk and grabbed her phone.

For a full five seconds, her finger lingered over the call button for the first person in her speed dial, but she quickly changed her mind and called the next person.

After two rings, a voice on the other end of the line said, "are you okay, Regina?"

The brunette let out a sigh of relief and nodded, before her slightly drunk mind remembered that the other woman couldn't see her, "I was wondering whether you would want to come over for coffee…."

"At half-eight at night?"

Regina blew out a breath and in frustration, "it doesn't have to be coffee, Kathryn."

A slight chuckle on the other end just made the mayor huff and roll her eyes at the same time.

"Why can't you have 'coffee' with Emma?" the blonde replied after a moment.

The brunette just rolled her eyes and waved her hand.

A moment later, purple smoke bellowed throughout the room and a very surprised blonde woman appeared, clutching her phone tightly to her face.

Kathryn blinked a couple of times before she took in her new surroundings and just sighed as she brought her phone down and ended the call.

"You could have warned me," she breathed, making her way across the room to pour herself a drink.

Regina threw her phone back onto the desk and followed the blonde over to get a refill.

A moment later, they each took a seat and Kathryn took a sip, raising her eyebrows at the silent woman. Regina made no move to empty any of her own tumbler, and instead simply sat staring into the amber liquid as if she was contemplating something profound.

"Is there something you wanted to talk about?"

The brunette finally looked up at her guest, almost as she was surprised she was there and said, "is there an issue with me wanting company?"

The blonde rolled her eyes and placed her drink onto the coffee table, "you only poof me here when there is something really bothering you, which means that Emma did something stupid…"

"She didn't do anything stupid," the mayor sighed, "the sheriff is not bound by any kind of contract to stay after dinner and watch a movie with me and Henry…"

Kathryn smirked at the bitterness in her tone and replied, "I'm guessing that you want her to have to stay?"

"Of course not!"

The other woman held up her hands to placate the brunette and just smirked harder at the defensiveness in her tone, "okay, so you want her to have wanted to stay?" Kathryn took the mayor's lack of eye contact as confirmation and continued, "you can't act like her girlfriend without asking her out, Regina."

"I have never said that I want to be with the saviour, Kathryn," Regina said through gritted teeth, trying to ignore the eruption of butterflies in her stomach at the mere thought. "There is no logical way that the relationship would ever work…"

"Love is not logical."

The brunette finally made eye contact as she narrowed her eyes at her friend, she only narrowed them further when she saw the full on smirk on her face.

"I don't love Emma; I merely have strong feelings for her that will go away with time."

"Perhaps if you expect these feelings to go away, you shouldn't be hurt when she doesn't want to spend time with you."

Regina swallowed hard and nodded. It may have been a harsh truth, but it was precisely why she often called Kathryn when she was having Emma Swan related issues. In all honesty, she would much rather talk with her closest friend about all of this, but that obviously was not an option.

"If she says no then everything will change," the brunette whispered, looking back down at her lap.

The smirk fell away from Kathryn's face and she tilted her head as her friend brought the apple cider up to her lips and took far more than a sip. Though she had been warned about continuing her friendship with the mayor after she curse had broken, she had found that she had actually missed the woman during the months that she was isolated from the town. It was for that reason that she had been one of the first people outside of the Charming family to approach her. Simple run-ins turned into planned lunches and coffee and she now found that she liked being the person that former Evil Queen would turn to when she was having a non-magic related crisis. However, she also wished that there was some way that she could physically drag the woman to the sheriff's station and force her to ask out the saviour so that they could end their stupid façade of friendship. They were so obviously meant for each other and she knew that she wasn't the only one who was frustrated with the way that they danced around each other.

"Do you not want everything to change?" the blonde asked softly.

The brunette bit her lip, going back to staring into her drink.

For a second, she considered why she wanted Kathryn to be here, since every time this had happened, the conversation always went the same way. The other woman would just try and convince her to ask Emma out and they would end up going in circles until Regina had reminded fully of all of the reasons as to why she could never be with the saviour.

Kathryn looked at her expectantly for another few moments before she rolled her eyes.

This was exactly what she had expected to happen, though she was rather confused about the circumstances. Usually the brunette called her over after she had spent too much time with the object of her affections and was having a hard time maintaining her indifference towards her feelings. Now, though, Emma had left and that clearly hurt Regina more than not having her around.

"Have you asked her why she left?" the blonde asked softly.

The brunette looked up in surprise, almost as if she hadn't expected the conversation to continue and she shrugged.

"Henry asked me what bisexual is, so I explained it to him and admitted to him how I know so much about it…"

Kathryn watched as she worked through the implications, the former queen's eyes widened for a moment, before she dismissed the possibility. Emma had been in awe of the fact that she had legalised the right to gay and bisexual in the Enchanted Forest, there was no way that she could be homophobic…or at least she hoped.

The blonde across the couch from her began shaking her head as it occurred to her what Regina was probably thinking, "you can't honestly believe that Emma is uncomfortable with you being bisexual?"

The brunette shook her head, though she still had a worried expression etched upon her face.

Kathryn let out an exasperated sigh, before she tilted her head in thought. It seemed odd that Henry would have just randomly asked. It was especially weird that he would have asked at the dinner table, almost as if he wanted to ensure that both of them were there.

Instantly, she began forming theories about what was going on and after a few seconds, she began wondering what Henry's newest operation could be called.

 **A/N So this was just a random idea that I had and if you guys like it, I'll definitely continue it as a two-shot XD**

 **Let me know if you have anything that works against SwanQueen being together that Henry could fix haha**

 **As always I need to thank my beta, QueenApples for being overall awesome and PerditusFic for always listening to my very random ideas haha**


	2. Chapter 2

Chapter two

-Two days later-

"I think I may have made things worse…" Henry sighed, falling onto the couch that Emma had convinced the pirate to bring into his quarters on his ship.

Hook sat down next to him and raised one of his eyebrows in his signature move.

"And why is that, lad?"

"Ma left earlier than she usually does after dinner and I don't think that they had spoken to each other since…I think that I might have freaked her out a little. Maybe we came on too strong?"

Killian just shook his head and replied, "coming on strong may be the only option considering that you are trying to match together the two stubbornest women in town."

The younger of the pair sighed heavily, falling back against the couch, he lolled his head to the side and asked, "so how do we step it up? I mean, there was so many things that could be keeping them apart. How are we supposed to show them that none of them should matter?"

"We're just going to have work through each issue and hope that they will eventually work it out for themselves. It would be unreasonable for us to deal with everything for them, so we just need to pick the biggest issues first…"

Henry nodded his agreement and thought for a moment. He couldn't wait for a time when all of the barriers between his mothers wouldn't matter anymore, because they would be together and so in love that they wouldn't even think about what had been keeping them apart. But the fact remained that there were many issues in their way. For starters, there was the fact that Regina had devoted a lot of time to trying to make Emma's parents miserable, Regina was technically about sixty-years-old and she had cast the curse that had left Emma as an orphan for the first twenty-eight-years of her life. Both women were extremely insecure about love after everything they had been through in their lives and Henry could hardly blame them for being cautious. But it was seriously beginning to ignore him the longer they were just friends. He could tell that they both liked each other very much and he had to find a way to make sure that they could see that too. He was getting sick of them claiming they were friends when they already basically acted as though they were married.

"What should we go for first?" the boy sighed as it occurred to him just how many things were keeping them apart.

Killian shrugged and replied, "perhaps the most obvious issue is that of Snow and Charming…"

Henry frowned for a moment and said, "but they've accepted mom…they treat her like one of the heroes…"

"Treating the woman who made their lives miserable for decades as an ally is one thing, but accepting her as their daughter's girlfriend is another thing entirely. We need to figure out just how they would react to the news. I believe that this would certainly be something that both of your mothers would be worrying about. Emma hasn't had parents for long and she probably doesn't want to do anything that could put their relationship at risk and Regina wouldn't want to take a part in tearing them apart again."

The brunette nodded slowly, he hadn't really considered just how his grandparents would feel if Emma and Regina were to get together. He could imagine that they would probably be shocked at first since they were usually the last people to notice what everyone in town already knew. But he also had no doubt that they wanted nothing more than for Emma to be happy and that a relationship with Regina would be the saviour's happy ending. Therefore, they should have no real objection to the relationship. Of course, that all very much hinged on how much they truly believed in Regina. It was very possible even though appeared as though they were friends with her, the pair of them held ill feelings towards her for what happened in the past. They did have every right to do so, though, which meant that Henry could only hope that they wouldn't be the thing that made his operation completely fail.

"Do you think that they would be against it?" he asked sheepishly, hoping that everything his mind had just worked through was not true.

Killian shrugged again before he replied, "I don't pretend to know the inner thoughts of the Charmings, lad. But anyone can get used to something given time, so maybe giving them some kind of warning as to what could be coming would make their potential reaction less…hurtful?"

Henry thought about this for a moment, thinking about how that conversation would go. He had long ago noticed that Snow usually didn't react well, so he decided that it would be best to allow his grandfather to break the news to his wife so that she would have time to react to it in private.

"I guess I could do that…but how would that get back to my moms?"

"Your grandparents do enjoy making their feelings known, so I'm sure that one of them will blurt it out to Emma once they figure out just how they feel about the prospect of her being with Regina."

"And if they can't deal with it?"

"Then I'm afraid that our operation may have already failed," the pirate sighed.

* * *

Henry tapped his fingers on the counter as he continued to look at the diner door.

He was more than grateful that David had agreed to have lunch with him the very same day as his conversation with Hook, since he couldn't imagine that he would be able to handle worrying about his reaction for long. Killian had dropped him off at the diner and had asked Ruby to watch him while he waited for his grandfather. It had been exactly five minutes and he could already feel his anxiety building as he wondered how he could possibly start the conversation.

Before he could think more about this, though, the bell over the door rang out. He swallowed hard, but the tension quickly fell away when he saw that it wasn't the person he had been waiting for.

The boy offered the blonde woman a small smile as she approached the counter, which she returned.

"Hey Kathryn," Henry said, turning around so that he was no longer facing the door.

"Hello Henry," the woman returned, before motioning to Ruby, silently asking for her usual order of coffee, which the brunette set to work making. "Are you alone?"

The boy shook his head, "I waiting for David to come and have lunch…"

"So why do you look so nervous?" she asked with a furrowed brow, "surely you've had lunch with your grandfather before…"

The brunette bit the inside of his cheek and internally berated himself for being so obvious, before he replied, "I just have something important to ask him and I don't know how he's going to react."

"Is this for your operation?"

Henry opened his mouth to say something, before her words finally registered and his eyes widened, "w-what operation?"

The blonde laughed and shook her head, replying more quietly this time, "your mother told me what happened at dinner the other night and I can only assume that you're planning something. I'm fairly certain that you already knew what bi-sexual means, Henry, so obviously you wanted your mother to admit something in front of Emma."

"My mom told you what happened?" he asked with a furrowed brow.

"She tells me everything that happens between her and Emma."

"Really?" Henry blanched.

Before Kathryn could say anything, she heard the clicking of heels, which meant that her coffee was ready and looked up to Ruby with a smile.

"Thank you," she said, accepting the beverage and placing a few notes on the counter.

Ruby nodded and took the money, walking off to put it in the till.

"Women tend to want to talk to their friends about their crushes," she whispered by way of reply to Henry's question, before she turned on her heels. Henry was about to say something, but she quickly added, "I really should get back to work, but do let me know if there is any way that I can help. I really am sick of being poofed to the mansion."

The brunette boy furrowed his brow at the last part, but she was already walking away before he could question it. He blew out a breath of relief as he realised that Kathryn had just confirmed one of the things he had been most worried about, his mother definitely did like Emma and somehow it was comforting to hear that the usually composed mayor poofed her friend into her home to rant about how she felt for the sheriff. He smiled slightly when he thought that the former queen would be frustrated at the ever-childish woman in a different way when the two of them finally got together.

Before he could think any more on this, he looked back up to the door and smirked slightly as he saw David awkwardly say 'hello' to Kathryn on the way out.

After a few seconds, the prince approached the counter and smiled at his grandson and they silently agreed to go over to the booth that they usually sat in.

"Thanks Rubes," David said after she placed menus in front of them, "but I think that we'll both just have our usual's."

The waitress just rolled her eyes and reached down to collect back what she had just put on the table, "I honestly don't know why Granny bothers having the menus printed, everyone just orders the same thing every single day…"

Henry and David smirked at her mini rant as she walked back over to the table and the older of the pair looked back over to his grandson, "did something happen?"

"I think she was late to work because she wanted to spend more time with Belle and Granny yelled at her."

The blonde laughed lightly, knowing full well that Granny and Ruby would probably make up later once the diner was no longer busy. Once his amusement fell away, he remembered what that Henry had sounded somewhat worried on the phone when he had invited him to lunch, which was why he had rushed over to the diner as quickly as possible. He honestly had no idea what his grandson could possibly want. Everything seemed to be going pretty amazingly well recently. They hadn't had any crises since Belle had sent Mr Gold over town line. Everything had been unusually peaceful, so he was rather anxious if Henry knew something that could end Storybrooke's current tranquillity.

"So…" the deputy began, looking over to the boy expectantly.

Henry swallowed hard as he was reminded that there was a reason that he was here other than having lunch with David and he noticed just how worried the man looked.

"I just wanted to ask how you would feel about something…I would like to think that you would be okay with it…but if you and Snow aren't, then it could ruin everything…so I really hope that you'll be okay with it…"

Charming held up his hand to silence the brunette, who quickly clamped his mouth shut and looked at the man apologetically, knowing instantly that he had probably just confused him further.

"Unless you tell me what it is, Hen, then I can't tell you if I would be okay with it."

Henry took a deep breath and nodded, before he said, "I really don't know how to say this…so I'll just come right out and ask. How would you feel if my moms got together?"

The blond opened his mouth, allowing it to hang open for a moment, before he quickly closed it. This was certainly not what he had expected, but it wasn't the concept that he was shocked by, it was more that his grandson also knew about the possibility.

"You've noticed that too?" he finally asked after a few seconds of silence.

The boy blinked a few times as he worked through each word of the man's reply, trying to figure out if there was something he was missing.

"You know…" Henry sighed, finally realising exactly what he meant.

"I've known since Neverland…it was pretty difficult to miss, but I still needed time to come to terms with it…"

"And you've had enough time?" the boy asked timidly, hoping beyond hope that he wasn't about to be told that he would object wholeheartedly to their relationship.

"It's hard to deny just how perfect they are for each other; I've been okay with it for a long time. Which is why I've been quite shocked that they haven't gotten together yet and I haven't had to tell Snow that I've known for so long…"

Henry smiled at the news, before his smile feel into a frown and he asked, "grandma doesn't know?"

Charming laughed lightly and shook his head reassuringly, "she certainly didn't figure it out when I did, but she has known for quite sometime. During the missing year, it was obvious that it wasn't just you that Regina missed. Snow ranted at me for hours over it and I spent hours trying to convince her that it would all be fine and that we should give our blessing if they ever had a relationship. It took a while, but she eventually agreed and we have been waiting for something to happen, so that we could reassure them that we would be okay with it. But then Regina got together with Robin and Emma with Hook for a while…I thought maybe we were wrong…"

"But you know you're not, right? They belong together and I don't get why they're just pretending to be friends when they know that they can be so happy together…"

"Love is not logical, Henry, though it may seem as though it is to onlookers. We might not understand what is keeping them apart, but we have to respect that they need time to work through whatever it is…of course, I'm sure they have had more than enough time…perhaps one of your operations is in order?"

Henry smirked at his answer, instantly relieved at what he had been told and nodded, "it's already in the works…."

Charming chuckled lightly and asked, "and what is it that Snow and I can do to help?"

"Maybe find a way to casually tell Emma that you would be okay with her being with my mom?"

"Casual isn't exactly our speciality…" David frowned, trying to remember the last time that he and his wife had been subtle.

"Could you try?"

"I suppose…but there is a chance that Emma will find out about your operation…" he replied.

Henry shrugged and said, "it's okay, she already knows. Maybe you and grandma can convince her that she should actually help make it work…"

 **A/N Reviews would be much appreciated XD**


	3. Chapter 3

Chapter three

Emma absentmindedly scrolled through her phone, hoping to find something of interest as she lay listlessly on her parent's couch.

She hadn't actually spent this much time in the apartment that she technically lived in for a while since was normally at the mayoral mansion when she wasn't at work. More often than not, she had ended up sleeping in the spare room and even had a duffel bag of clothes stored in what had been dubbed her room, which was something she had been surprised Regina hadn't objected to. Of course, she had also been rather surprised that her parent's hadn't complained about the amount of time that she spent over there since they had seemed pretty obsessed with spending as much time as possible with her after the curse had broken. The pair did still take every opportunity to spend time with her that they could, but they no longer awkwardly tried to awkwardly insert themselves in her life.

It was for this reason that she was somewhat more surprised than she would have been in the past that she could feel Mary Margaret and David staring at her from the kitchen as they whispered. She could tell that they were planning something and she was originally content with waiting for them to come to her with whatever they wanted, but she was unbelievably bored right now. So she propped herself up on her elbows, looking over the back of the couch and gave them each an expectant look.

The motion caught their attention and they both immediately stopped whispering, looking as though they had been caught doing something terrible.

"Is something wrong guys?" she asked with a tilted head, pushing herself into a sitting position.

David and Mary Margaret exchanged a quick, silently arguing that this was a bad idea, but they also each knew that it was now far too late to go back. Their daughter certainly knew how to be suspicious and it didn't help that she would know if they tried to come up with some excuse for their odd behaviour.

"We…we were just…" Snow began and Emma raised an eyebrow at her mother, who sighed and said, "we have something important to discuss with you, but we don't know how to…broach it…"

Emma thought back to what had happened during dinner with Regina and she instantly had a bad feeling that this had something to do with Henry's newest operation, though she hoped against hope that it didn't. She would be lying if she didn't say that her parents were a big part of why she couldn't just ask Regina out on a date, but there were many other reasons. She never wanted things to get awkward with Snow and David, since she finally had the parents that she wanted, especially if they were never able to get used to the idea of the former Evil Queen and the saviour.

Taking a deep breath, she tried not to show them just how worried she was and pushed herself off the couch in order to walk over to the kitchen counter. After a moment, she slid onto one of the stools and looked between the brunette and blond.

"Is it something serious?" she asked, pretending to have absolutely no inkling as to what they could be talking about, since she sincerely hoped that she didn't.

"No... well, it shouldn't be, but it kind of is…" Snow rambled, looking to her husband for help, but he didn't seem to have any idea how to start the conversation either.

Emma looked between them and stopped herself from rolling her eyes. The pair were acting strange, even for them, and she said, "what is it?"

Snow swallowed hard and replied, "David and Henry were discussing something important at lunch and he asked us to reassure you of something…"

Emma closed her eyes in frustration and pinched the bridge of her nose. She knew that Henry was conducting some kind of operation, but she doubted that he understood just what he had done. Even though neither of them looked in any way angry at the prospect, she couldn't help the nagging feeling at the back of her mind. They obviously wouldn't tell their grandson that they wouldn't want his mothers to be together. But then again, they weren't particularly the best at hiding their feeling and Henry probably wouldn't have let her go and talk to them if he knew they were going to say something he didn't want them to.

Blowing out a breath of frustration at all of her conflicting thoughts, she decided that there was absolutely no way that she was getting away from this now. At least this could help to alleviate some of the worry that she had been feeling once she realised how she felt about Regina. A huge part of her knew that the Charmings would never want to lose her, but she had grown accustomed to doing something that would make foster parents not want her. Falling in love with her ex-step-grandmother, who also cast the curse designed to take away everyone's happy endings was something that she would imagine would at least make them doubt her judgement.

Gritting her teeth, she asked again, "what is it?"

David blew out a breath of exasperation when she saw the worried look on her daughter's face and replied, "he asked me how we would feel about you and Regina entering into a romantic relationship…"

Emma sighed deeply resolving to actually tell the boy off, but she knew that if she left now, she would only worry about what they were going to say. So she just nodded her head and looked at them expectantly, completely unable to think of any sort of verbal reply.

Snow inspected her worry and instantly felt bad that they hadn't done this earlier. Her and Charming had spoken about this at length once they both knew that it was a possibility. When they had gotten past the sheer weirdness of the prospect, it became clear that it made absolute sense. They complimented each other perfectly and they already shared a son, so they decided that they wouldn't get in the way of any attempt the pair made to embark on romantic relationship. In fact, they had actually assumed that they were already together in secret at times considering how much time they spent together. But then Hook and Robin had happened and it no longer looked likely.

Now that they had both broken up with their boyfriends, it seemed completely ridiculous that they had yet to even acknowledge their feelings for one another.

Steeling her nerves, Snow reached forward to place her hand over the blonde woman's and squeezed as reassuringly and she couldn't help but smile when she noticed that her daughter relaxed marginally.

"Sweetheart, you do know that we would never stand in the way of something that would make you happy…"

Emma averted her eyes to the table, she could feel a stabbing in her stomach when she realised that they were not reacting in disgust. It both confirmed that neither of her parents had a problem with her sexuality (which many of her foster parents had a huge problem with) and that they would be okay with her being with Regina. Honestly, her mind was having a hard time dealing with all of this acceptance. Every time she had played this conversation through in her mind, she had gotten complete rejection. She had imagined that they would threaten to disown her if she didn't pretend that she didn't have feelings for Regina.

Plus, there was the issue that there were many more problems with a potential relationship with the former Evil Queen, not least the fact that she didn't actually know for a fact that the woman felt anything for her.

It was for this reason that she decided to go for denial inside of thanking them for all this meant to her.

"I don't know what you guys are talking about…" the saviour replied, though she was refusing to make eye contact with either of her parents, as she brought her hand away from her mother's and into her lap.

Snow and Charming exchanged a look of concern and the male of the pair said softly, "you don't need to lie to us, Emma, we've known for a while…"

The blonde took a deep breath and shrugged her shoulders dramatically, "I really have no idea what you're talking about. I haven't really had a chance to even think about having a crush on anyone with all of the crises. Why would I lie about it?"

The three of them fell into silence as Snow and David tried to figure out why she was lying.

After a few seconds, David decided that she probably didn't know the answer herself and that they should probably go with it until she managed to figure it out.

He nodded and replied, "of course you wouldn't lie, but we just wanted you to know that we wouldn't have an issue with anyone you want to be with. As long as they make you happy, as Regina obviously does, then we will be perfectly accepting of the relationship."

Emma sighed exasperatedly and replied shortly, "okay, thanks…I really need to go…"

Snow furrowed her brow and looked over to the couch that she had been laying listlessly on. She knew that her shift at work didn't start for another three hours and Henry had insisted on being watched by Killian today, so by all rights there was nowhere that she had to be. Usually, under these circumstances, she would go and have lunch with Regina, but since she hadn't talked to the woman in days, she was obviously trying to fill her time away from work unsuccessfully.

"Where?" the brunette woman asked, tilting her head questioningly.

"I…need to go and talk to Henry about something," she replied, raising from the stool, already thinking of how she was going to berate her son.

Before either of them could tell her to go easy on the boy, she had already walked across the apartment and picked up her car keys.

Both of them sighed in unison as the door shut behind the woman and David turned to his wife, "that didn't go well at all."

Snow nodded her agreement, running a hand across her face in frustration and replied, "well you did warn Henry that it wouldn't…"

"I did promise that we would try and be subtle…I'm pretty sure that was the complete opposite. I mean, it wasn't even as if we slipped it into a conversation."

"We're going to have to make it up to him, somehow," Snow replied, pushing herself from the counter, going to check on Neal.

* * *

"Henry!"

The boy instantly jumped from the couch and looked over at the pirate with wide eyes. The pair of them had been taking a break from the operation and he had decided that it was time to explain the MCU to Killian. After about twenty minutes of confusion, he had just pulled his laptop out of his bag and put Iron Man on. The movie only served to confuse the man further and he had just been in the middle of explaining that it wasn't actually possible, when his blonde mother's voice had interrupted.

Killian leaned forward and pressed the spacebar to pause the movie and then closed the lid, something that he was rather proud to have remembered, and looked at the boy in sympathy as the saviour finally appeared at the door to the captain's quarters.

Emma's eyes moved between the pair, both of whom looked incredibly guilty and said, "can I have a minute with Henry, Hook?"

"You do know that this is my ship, love?" Killian asked with a small laugh, though his movement towards the exit seemed to suggest that he wasn't actually interested in arguing with the saviour.

"You go back to whatever you were watching in a minute, I just need to talk to my son for a minute," Emma replied, keeping her narrowed eyes on the very nervous looking boy.

Killian just nodded and came to stand by the door a moment later. Placing his hand on the woman's shoulder, he whispered, "go easy on him, Swan," before he slipped out and resolving to go and find something to do rather than eavesdropping. He would rather not be in the woman's line of fire for anything and he also wanted to be able to continue with the operation plans since he could no longer stand the saviour and former Evil Queen skirting around each other like a couple of insufferable teenagers with crushes.

Once the blonde was satisfied that the pirate was gone, she stalked over to Henry slowly and then fell onto the couch, silently telling him to do the same as she looked up at him.

Henry swallowed hard again and sat down gingerly, before he asked, "did something happen, ma?"

Emma rolled her eyes, knowing that he was only feigning ignorance and said, "when I told you how I felt about your mother, it was because I needed to tell someone. If I had thought that it would have been a good idea to tell my parents, then I would have told them. The reason that I didn't was because I wanted to avoid a very awkward conversation about something that is never going to happen."

The brunette nodded. It was immediately obvious that everything had gone to plan. He had known that his grandparents were completely incapable of subtlety, but he also knew that it was a major issue to check off the list.

"Did they say something bad?" he asked.

Emma took a deep calming breath and shook her head, "they said that they would be okay with whoever I want to be with as long as they make me happy..."

"So why are you mad at me?"

"Because I told you that I wanted you to drop it. I didn't want your help on this and I definitely didn't need one of your operations," she shot back, though Henry easily ignored the bite in her tone.

"If I leave it to you, then you and mom are going to be miserable until one of you stops being stubborn and just goes for it. I know for experience that you can both be stubborn for a long time, so I just want to make sure that you don't waste your time again with other people. Mom wasn't happy with Robin and she felt so guilty about it because she believed that he was supposed to be her soulmate…"

Emma clenched her jaw at the mention of the thief and his stupid tattoo, but she quickly tried to move past it. She had been set to ask Regina out when she returned from New York. When she had gotten her memories back, she knew exactly what she needed to do. But when she had found out that they were all missing a year of memories, she had resolved to wait until that was all sorted out. When Regina had told her about Robin, she had started to berate herself endlessly. If she told Regina how she felt after that, then she would be the selfish person trying to break apart soulmates. She had been so worried that the man would return from New York any day now, since soulmates 'always found each other' and she wished desperately that there was something that could stop her thinking about him.

Henry inspected her expression and he smiled slightly when he realised that Hook had been right about one of the things they would have to address. Soulmates had never been something that the boy had ever put much stake in since he was always a firm believer in True Love. It was for that reason that he felt as though he was the only one who allowed himself to admit that he didn't really think that Regina and Robin together was a good match. They were certainly good together, but they seemed to be missing vital chemistry. Their conversations were never interesting battles of wit and he wasn't convinced that Robin would ever be able to trade barbs with the former queen in the same way that he had seen her and Emma did. Even if he didn't quite understand what was hiding behind the heated conversations that he had seen them share, he knew that there was no way that it could be purely platonic.

The blonde pinched the bridge of her nose and said, "you are going to drop this operation and if I catch you doing anything else, you will be grounded until college."

Henry's mouth fell open, "that's so not fair."

Emma held up her finger before he could say anything else and said, "just do as you're told, Henry."

"And how would you explain to mom why you're grounding me?" he shot back as she rose from the couch to take her leave.

The saviour closed her eyes in frustration and didn't even turn to face him before she said, "I'll find a way, so don't test me."

The brunette dramatically fell back against the couch, folding his arms and mumbling, "fine, I promise that I won't do anything else."

Emma furrowed a brow and thought to question the way he had said that, but she knew that she needed to get ready for work, so she just nodded and walked towards the exit.

Henry remained in his petulant position for a few moments, before Killian returned with raised eyebrows.

"She doesn't look too impressed lad," he said, returning to the couch.

"She made me promise not to carry on with the operation," Henry sighed.

Hook furrowed his brow and tilted his head as he inspected the boy, he had seen him after he had been told that he could do something and he certainly look as bothered by the fact as he should have been.

"You seem oddly okay with that…" he said.

Henry pushed himself up as replied, "I knew that Snow and David wouldn't be subtle, but it had to be done…but ma said that I couldn't do anything, she didn't say anything about other people."

Killian laughed lightly and leaned forward to lift the laptop lid, "you truly are Rumpelstiltskin's grandson."

 **A/N Reviews and suggestions would be much appreciated XD**


	4. Chapter 4

Chapter four

Regina frowned down at the two cups of to-go coffee in her hands and she wondered whether she had ever been this nervous in her life, especially when it came to Emma Swan. She had certainly been somewhat nervous when the woman had first shown up in town considering that she symbolised the possibility of losing her son and her cursed life. Now things were different though and rather than wishing that the saviour would just leave town she was wishing that she would be able to just go and spend time with the infuriating blonde.

It hurt more than she thought possible when she had realised that she hadn't seen her best friend in days and what was worse yet, she had no idea what was keeping her away. She knew that it had something to do with what she had admitted to Henry the last day she had seen her. She had of course thought that it must have something to do with her admission of bi-sexuality, but her mind was having some trouble figuring out what it could be. Either Emma was homophobic, which she was pretty sure was not possible, or she had rushed out because she had been freaked out by Regina herself not being straight.

The brunette quickly shook her head, trying to force all of her worries to leave her mind as she pushed the door to the sheriff's station open.

After a short walk down the corridor, she swallowed hard as she came to the main area and her eyes were instantly drawn to the office at the other side, where a certain blonde was visible. In her concentration, Emma hadn't even noticed that another person had entered and she held up a scrunched up piece of paper, trying to angle it perfectly. Regina watched with a quirked eyebrow as the woman finally threw the paper, which went straight into the waste bin without touching the side.

The mayor chuckled lightly and began walking over to the sheriff's office while the childish woman did a little victory dance at her desk.

"Our tax dollars hard at work I see," Regina smirked while she leaned against the doorframe.

Emma's mouth dropped open slightly and she looked up at the older woman, looking very much like a deer caught in headlights.

"Regina…" she breathed with her expression halfway between anxious and happy. She was more than missing Regina, even if the very thought of seeing her had made the saviour's mouth go dry. She thought that it would be easier to not think about her crush if she didn't have to see her unfairly beautiful face as often as she usually did, but honestly it was probably making it worse. All she thought about was trying to find some random piece of paperwork so that she had an excuse to go to the mayor's office and it made her so happy to see that the former queen hadn't even bothered with pretence. They usually planned when they were going to have coffee together, but the other woman had obviously taken the initiative and the blonde felt her stomach erupt in butterflies when she wondered whether the brunette had missed her as much as she had missed her.

Finally, the blonde woman realised that Regina was looking at her expectantly and she quickly thought of a reply, "you've already used that one, madam mayor."

"I believe it applies quite aptly," the brunette chuckled lightly.

Emma chuckled too and Regina walked over to the desk to place the coffee upon it.

"I can see that you're very busy, but I assume that you have time to have one drink."

The blonde was about to nod her agreement, before she realised that having coffee with Regina would mean that she would actually have to sit down and have a real conversation. She wasn't sure whether she would be able to get through the whole thing without mentioning what she had found out. In that very moment, she actually wanted to blurt it out.

"Actually…I have a meeting…" Emma said as convincingly as possible.

Regina frowned for a second as she looked over her shoulder at the trash bin surrounded by balled up pieces of paper.

"With who?" she asked disbelievingly.

The blonde bit the inside of her cheek and desperately ran through all of the people that she could possibly have a meeting with, but it wasn't exactly like she could lie about town hall business to the mayor herself.

But then it occurred to her that there was something that wouldn't exactly be a lie, assuming that the person that she needed to talk to was actually available.

"The events coordinator for the winter festival wants to meet with me to discuss what would be expected of the sheriff's department during the event."

Regina narrowed her eyes for a moment. She knew that the woman wasn't telling the complete truth, even if that was something that she had to do, she certainly didn't have to do it this very second.

"You have a meeting with Alex?" the brunette asked.

The saviour frowned and asked, "Alex?"

"The events coordinator for the festival…"

"I thought Thomas was doing it…" the blonde sighed as she practically felt her cover story collapse around her.

"Alex wanted the experience and Thomas decided that he would rather go to the festival this year," the mayor replied, her eyes narrowing further as she explained.

"Well then I guess that it's Alex that I'm meeting with," Emma said as she stood from her desk chair. "We can have coffee another time, Gina."

The brunette watched her go and considered that she could offer to walk over to Town Hall with her, but she was pretty sure that she wouldn't be able to take the thought of more awkwardness, so she instead just nodded.

Emma offered her a quick wave and a smile as she thanked the other woman for the beverage and then just about stopped herself from running out of the station. Once the saviour was out of sight, she leaned against the nearest wall and pinched the bridge of her nose.

"You're an idiot, Swan," she muttered.

* * *

-Later that day-

Henry blew out a breath of frustration as he walked up the drive towards the mayoral mansion. He looked over his shoulder and quickly offered Hook a wave goodbye before he pushed open her door and allowed his backpack to drop to the ground.

They had spent the whole day trying to plan a way to get the saviour and former Evil Queen to finally admit their feelings for each other, but nothing seemed like a good idea. He had suggested arranging a lunch date by convincing both of them that they would be meetings someone else, but Killian had pointed out that there was great potential for awkwardness if they went that route. This also seemed to be true for most of the other things that he suggested since they almost all resulted in both of his mothers ending up in a situation that they hadn't planned for themselves.

He couldn't help but think that his grandfather had been right in saying that he shouldn't meddle in matters of the heart, especially since he didn't understand exactly what was keeping them apart.

"Henry?"

The boy looked up to the direction that the sound was coming from and instantly allowed his feet to carry him towards the kitchen.

When he appeared in the doorway, Regina quirked an eyebrow at said, "I thought you were coming home in an hour."

"Killian forgot that he planned to have dinner with ma…he did invite me but I thought that you would have probably already started dinner," he replied as he came over to the counter upon which his mother was chopping vegetables.

Regina nodded and looked back down at the carrot before a loud chop filled the room and Henry's eyebrows shot up in surprise.

"What did the carrot do to you?" he asked.

The older brunette blinked a couple of times and sighed before she placed the knife down and shook her head,

"I'm just a little…on edge," she replied.

Henry tilted his head for a moment before he moved forward to take a seat on the opposite side of the counter to his mother. He could tell from her facial expression and how tense her shoulders were that her words were true and he also had a feeling that he knew exactly why she felt so on edge.

"Is it because of ma and Hook going for dinner?"

Regina furrowed her brow at the mention of the pirate. She had initially hated him when it appeared as though he and Emma were set for a relationship, but her hatred had faded almost as quickly as their romance. It soon became apparent that Killian was actually a good man who her son needed in his life after Neal had died. She didn't want to imagine how Henry would have dealt with the loss of his father without the support of Hook. Her and Emma wouldn't have been able to provide the same kind of support in their capacity as his mothers and the more time that Henry spent with the pirate, the more that Regina started to like him. Since the curse had broken, she had learnt that if Henry was an excellent judge of character (with the exception of Peter Pan of course, but she tried not to think about that too much).

"They have dinner all the time, Henry, it's not an issue," she replied as she slowly picked up the knife to resume her chopping. She didn't really want to discuss the infuriating blonde since she had no idea what had suddenly gone wrong with them.

"So…what's wrong?" Henry asked and pulled a piece of carrot from the safe zone of the chopping board. When Regina made no attempt to reply, he added, "is it because ma hasn't come here in a few days?"

The older brunette took a deep breath, she didn't really want to talk to her son about this since she didn't want him to know that she had been so bothered by not seeing the blonde in a few days. There was no obligation for Emma to come to the mayoral mansion every day for dinner, they were not together and she was still fulfilling her motherly duties to Henry. They were just friends and not girlfriends, she shouldn't be this frustrated at not seeing her 'friend' every-day. Though she had to admit that it hurt earlier when the sheriff had refused to have coffee with her.

"She is under no obligation to attend dinner here," she replied tightly and as evenly as possible.

Henry raised an eyebrow at the woman who was refusing to look up from the vegetables she was currently assaulting. If he had any doubt about the mutual attraction between his mothers, it certainly now gone. There was no way that he could deny the fact that Regina had strong feelings for Emma, which could only mean that what Kathryn had told him was absolutely true. A small smirk overcame his face at the thought of Regina ranting to Kathryn about her 'crush' on Emma just as Emma would have been ranting to him or Hook about her own feelings.

The boy was about to make a suggestion, but then he remembered the threat that his mother had made just a few hours earlier. He had told Hook exactly what he had to do and now he couldn't get involved anymore. As much as he knew that Emma's grounding threats would disappear the moment that she and Regina got together, he couldn't risk them becoming a reality before the operation was successful.

"I'm gonna go and do my homework," he announced after a moment of silence.

Regina frowned but still nodded. She had been almost certain that there was some kind of operation going on and she had been sure that Henry was moments away from telling her. At least if she knew exactly what he had done, she would know that Emma wasn't avoiding her because of something she had done. Of course, she didn't know that her son was working under the threat of a five-year grounding.

* * *

Killian offered Emma a final wave as she exited the diner and brought the coffee he had ordered up to his mouth. As he had promised, he had not once mentioned Regina or the operation, no matter how much Emma had tried to prompt him to give her clues. Even though the blonde had forbidden the operation to go forward, she had clearly not thought that it would have actually been effective. It was for that reason that Hook had tried to stick to his word and maintained that Henry had listened to her and given up on Operation Wingman. Luckily, he had managed to word it in such a way so that the Saviour's infernal superpower was not activated, though he could tell that she was still suspicious. However, he was also sure that she seemed somewhat disappointed that there was apparently no longer an operation for her and Regina to be together.

As the pirate placed his mug back down onto the table another blonde slipped into the booth opposite him and he smiled at her. The last thing that Henry had done for the operation was to inform Kathryn that she could talk Killian to coordinate and they had set up a meeting for after Hook had dinner with Emma to make sure that she thought the operation was over.

Kathryn returned the smile, though it was slightly tight. The two of them had never actually met, which made it very strange for them to meet to talk about such an important matter.

"I take it that you received Henry's message?" Hook asked.

The blonde nodded and replied, "he said that he's not allowed to help anymore and it's up to us."

Killian frowned, he had hoped that Henry would have sent a full plan to the woman since he had absolutely no idea what he was supposed to do next, but Henry probably didn't really know either. The boy was probably relieved that he could leave this in other people's hands.

Kathryn laughed at the nervous expression on his face as she thought about all of the stories she had heard about the great Captain Hook.

"I assume that Henry didn't give you any ideas either?" she asked, half exasperated and half amused.

Killian shook his head, "I think that he may be out of ideas at this point, probably why he was so willing to listen to Emma…"

Kathryn sighed and nodded, even if she had wanted Emma and Regina together as soon as possible that didn't mean that she had any ideas. Of course, she had considered forging a note from the mayor so that she could force them to have a meeting or a lunch date. But that plan hinged on the idea that Emma would actually show up to any of these meetings since she was currently avoiding Regina like the plague.

"The first thing we need to do is make them act like friends again and then we can work on getting one of them to ask the other one out," Kathryn pondered.

"And how do you suppose we are going to do that?" Hook asked with a frown. Getting the two most stubborn women in town to do what they wanted wouldn't be the easiest part of their operation.

"Absolutely no idea," Kathryn sighed.

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